Food Science and Biotechnology

Korean Society of Food Science and Technology (한국식품과학회)
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Analysis of Volatile Compounds and Enantiomeric Separation of Chiral Compounds of Dried Sancho (Zanthoxylum schinifolium Siebold & Zucc)

  • Published : 2009.02.28
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Abstract

The volatile compounds of dried sancho (Zanthoxylum schinifolium), an aromatic plant were extracted by simultaneous distillation and extraction (SDE) method and identified by gas chromatograph-mass spectrometry (GC-MS). Selected chiral constituents of sancho oil were characterized by enantiodifferentiation using multidimensional gas chromatograph (MDGC)-MS. A total of 57 compounds were identified and quantified, and the major compounds were identified estragole, nonanoic acid, octanoic acid, $\beta$-phellandrenene, and limonene. Among them, estragol (63.9%) was found as the predominantly abundant component of sancho. $\alpha$-pinene and nerolidol, and $\beta$-pinene and linalool were determined to be enantiomerically pure (100%) for their (S)-form and (R)-form, respectively. The enantiomeric composition of limonene in sancho revealed 83.9% purity for the (S)-enantiomer, whereas (E)- and (Z)-rose oxides showed mixtures of both enantiomers. The enantiomeric excess (%) for citronellal was 22.6% with the (R)-enantiomer as major enantiomer. The enantiomeric composition of these compounds can be used as parameter for authenticity control of sancho.

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References

  1. Choi YJ. The Korean Folklore Plants. Academybook, Seoul, Korea. pp. 191-193 (1992)
  2. Ko YS, Han HI. Chemical constituents of Korean chopi (Zanthoxylum piperitum) and sancho (Zanthoxylum schinifolium). Korean J. Food Sci. Technol. 28: 19-27 (1996)
  3. Janssen AM, Scheffer JJ, Baerheim SA. Antimicrobial activities of essential oils. A 1976-1986 Lature review on possible applications. Pharm. Weekblad 9: 193-197 (1978)
  4. Pattnaik S, Subramanyam VR, Bapaji M, Kole CR. Antibacterial and antifungal activity of aromatic constituents of essential oils. Microbios 89: 39-46 (1997)
  5. Grassmann J, Hippeli S, Dornisch K, Rohnert U, Beuscher N, Elstner EF. Antioxidant properties of essential oils: Possible explanations for their anti-inflammatory effects. Arznei.-Forschung 50: 135-139 (2000)
  6. Dang MN, Takacsova M, Nguyen DV, Kristianova K. Antioxidant activity of essential oils from various spices. Nahrung 45: 64-66 (2001) https://doi.org/10.1002/1521-3803(20010101)45:1<64::AID-FOOD64>3.0.CO;2-U
  7. Konig WA, Fricke C, Saritas Y, Momeni B, Hohenfeld G. Adulteration or natural Variability? Enantioselective gas chromatography in purity control of essential oils. J. High Res. Chromatog. 20: 55-61 (1997) https://doi.org/10.1002/jhrc.1240200202
  8. Ahuja S. Chiral Separations, Applications, and Technology. American Chemical Society, Washington, DC, USA. p. 201 (1997)
  9. Marchelli R, Dossena A, Palla G. The potential of enantioselective analysis as a quality control tool. Trends Food Sci. Tech. 7: 113-119 (1996) https://doi.org/10.1016/0924-2244(96)10011-X
  10. Schreier P, Winterhalter P. Progress in Flavour Precursor Studies. Allured Publishing Corporation, Carol Stream, IL, USA. p. 77 (1993)
  11. Mollenbeck S, Konig T, Schreier P, Schwab W, Rajaonarivony J, Ranarlvelo L. Chemical composition and analyses of enantiomers of essential oils from Madagasca. Flavour Frag. J. 12: 63-69 (1997) https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<63::AID-FFJ614>3.0.CO;2-Z
  12. Council of Europe. European Pharmacopoeia. 5th ed. Volume 1. European Directorate for the Quality of Medicines. Strasbourg, France. pp. 1894-1895 (2004)
  13. Weyerstahl P, Marschall H, Splittgerber U, Son PT, Giang PM, Kaul VK. Constituents of the essential oil from the fruits of Zanthoxylum rhetsoides Drake from Vietnam and from the aerial parts of Zanthoxylum alatum Roxb. from India. Flavour Frag. J. 14: 225-229 (1999) https://doi.org/10.1002/(SICI)1099-1026(199907/08)14:4<225::AID-FFJ818>3.3.CO;2-T
  14. Nikerson GB, Likens ST. Gas chromatography evidence for the occurence of hop oil components in beer. J. Chromatogr 21: 1-5 (1966) https://doi.org/10.1016/S0021-9673(01)91252-X
  15. Schultz TH, Flath RA, Mon TR, Enggling SB, Teranishi R. Isolation of volatile components from a model system. J. Agr. Food Chem. 25: 446-449 (1977) https://doi.org/10.1021/jf60211a038
  16. Sadtler Research Laboratories. The Sadtler standard gas chro.matography retention index library. Sadtler, PA, USA (1986)
  17. Davies MW. Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicone and Carbowax 20M phases. J. Chromatogr. 503: 1-24 (1990) https://doi.org/10.1016/S0021-9673(01)81487-4
  18. Stehagen ES, Abbrahansom F, Mclafferty W. The WileylNBS Registry of Mass Spectral Data. John Wiley and Sons, New York, NY, USA (1974)
  19. Robert PA. Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy. Allured Publishing Corp., Carol Stream, IL, USA (1995)
  20. Schurig V. Terms for the quantitation of a mixture of stereoisomers. Enantiomer 1: 139-143 (1996)
  21. Ruff C, Hor K, Weckerle B, Konig T, Schreier P. Authenticity assessment of estragole and methyl eugenol by on-line gas chromatography-isotope ratio mass spectrometry. J. Agr. Food Chem. 50: 1028-1031 (2002) https://doi.org/10.1021/jf011204h
  22. Bahk JR, Park SH, Kim JO, Kim SW, Lee SY. The effect of estragole identified and extracts form Agastache rugosa O. Kuntze on the fungal growth and metabolism. J. Food Hyg. Saf. 12: 63-70 (1997)
  23. Wan J, Wilcock A, Coventry MJ. The effect of essential oils of basil on the growth of Aeromonas hydrophila and Pseudomonas fluorescens. J. Appl. Microbiol. 84: 152-158 (1998) https://doi.org/10.1046/j.1365-2672.1998.00338.x
  24. Shin S, Kang CA. Antifungal activity of the essential oil of Agastache rugosa Kuntze and its synergism with ketoconazole. Lett. Appl. Microbiol. 36: 111-115 (2003) https://doi.org/10.1046/j.1472-765X.2003.01271.x
  25. Chae YA, Cho Mo, Song JS. Identification of chemotypes in traditional aromatic plant resources Z schinifolium Siebold et Zucco and Z piperitum DC. Korean J. Breed. 33: 126-132 (2001)
  26. Cho Mo, Kim H, Chae YA. Analysis of volatile compounds in leaves and fruits of Zanthoxylum schinifolium Siebold et Zucco & Zanthoxylum piperitum DC. Korean J. Med. Crop Sci. 11: 40-45 (2003)
  27. Lee Jo, Jang HJ, Kwag JJ, Kim OC, Lee GH. Analysis of volatile components of sancho (Zanthoxylum schnifolium) by solid phase micro extraction. Korean J. Food Nutr. 12: 119-123 (1999)
  28. Paula CSG, Manuel FF. Organ- and season-dependent variation in the essential oil composition of Salvia officinalis L. cultivated at two different sites. J. Agr. Food Chem. 49: 2908-2916 (2001) https://doi.org/10.1021/jf001102b
  29. Lee MS, Chung MS. Analysis of volatile flavor components from Zanthoxylum schinifolium and sensory evaluation as natural spice. Korean J. Soc. Food Sci. 16: 216-220 (2000)
  30. Belitz H-D, Grosch W. Food Chemistry. Springer-Verlag, Berlin, Germany. pp. 282-290 (1987)
  31. Kreck M, Scharrer A, Bilke S, Mosandl A. Enantioselective analysis of monoterpene compounds in essential oils by stir bar sorptive extraction (SBSE)-enantio-MDGC-MS. Flavour Frag. J. 17: 32-40 (2002) https://doi.org/10.1002/ffj.1033
  32. Ruiz del Castillo ML, Blanch GP, Herraiz M. Natural variability of the enantiomeric composition of bioactive chiral terpenes in Mentha piperita. J. Chromatogr. A 1054: 87-93 (2004) https://doi.org/10.1016/S0021-9673(04)01405-0
  33. Schurig V, Nowotny H-P. Separation of enantiomers on diluted permethylated $\gamma$-cyclodextrin by high-resolution gas chromatography. J. Chromatogr. 441: 155-163 (1988) https://doi.org/10.1016/S0021-9673(01)84662-8
  34. Fietzek C, Hermle T, Rosenstiel W, Schurig V. Chiral discrimination of limonene by use of $\beta$-cyclodextrin-coated quartz-crystal-microbalances (QCMs) and data evaluation by artificial neuronal networks. Fresen. J. Anal. Chem. 371: 58-63 (2001) https://doi.org/10.1007/s002160100899
  35. Ohloff G. Scent and Fragrances. Springer-Verlag, Berlin, Germany. pp. 43-44 (1990)
  36. Wust M, Rexroth A, Beck T, Mosandl A. Structure elucidation of cis- and trans-rose oxide ketone and its enantioselective analysis in geranium oils. Flavour Frag. J. 12: 381-386 (1997) https://doi.org/10.1002/(SICI)1099-1026(199711/12)12:6<381::AID-FFJ674>3.0.CO;2-5
  37. Dietrich A, Mass B, Karl V, Volker K, Peter DL, Weber B, Mosandl A. Stereoisomeric flavor compounds: Part LV. Stereodifferentiation of some chiral volatiles on heptakis(2,3-di-O-acetyl-6-0-tertbutyldimet hylsilyl)-$\beta$-cyclodextrin. J. High Res. Chromatog. 15:176-179 (1992) https://doi.org/10.1002/jhrc.1240150308
  38. Lorenzo D, Dellacassa E, Atti-Serafini L, Santos A, Frizzo C, Paroul CN, Moyna P, Mondello L, Dugo G. Composition and stereoanalysis of Cymhopogon winterianus Jowitt oil from Southern Brazil. Flavour Frag. J. 15: 177-181 (2000) https://doi.org/10.1002/1099-1026(200005/06)15:3<177::AID-FFJ887>3.0.CO;2-M
  39. Bonnlander B, Cappuccio R, Liverani FS, Winterhalter P. Analysis of enantiomeric linalool ratio in green and roasted coffee. Flavour Frag. J. 21: 637-641 (2006) https://doi.org/10.1002/ffj.1633